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As others correctly noted, as a landlord you must look at the big picture and if this happens to be a good tenant who has occupied the unit for a while, has a history of timely payments and has expressed interest in remaining at the property the value in an extension (assuming that is advantageous to you as the landlord) should be placed above your desire to collect rent in a certain method if this particularly tenant has strong desires to make their payments in a different manner....especially if the lease they signed allowed a different payment method.

Why sell for 90% of the value after closing costs, minus taxes.

I wouldn’t be excited paying much more than the land value.

What this tells me is Raleigh is likely better for long-term, conservative investments due to steady value growth.

Is the only way to pay for a Reno for my childhood home to sell my current home or is there a method I'm not familiar with that I can use my current homes value to help me out??

Great, What's your average value/door?

Plus you'll most likely make more money in home value growth compared to a multi family. 

As far as whether to approach them with or without an agent - approaching them directly without an agent can save the seller probably 2.5-3% of fees, which give you some room to negotiate on the price, but you need to be confident that you are capable of evaluating the property value, estimating on the amount of work that is needed, knowing how to negotiate/ structure the deal, and navigating the closing process.

For flips, calculate the after-repair value (ARV) and subtract purchase, rehab, holding, and selling costs.Pay attention to location, rental demand, and the property’s condition.